Cyclic ketone



United States Patent 'CYCLIC KETONE Lee C. Cheney, Fayetteville, andWilliam B. Wheatley, Syracuse, N.Y., assignors to Bristol LaboratoriesInc., Syracuse, N.Y., a corporation of New York No Drawing. ApplicationAugust 16, 1957 Serial No. 678,532

1 Claim. (Cl. 260-586) This invention relates to a new series ofunsaturated ketones having utility as medicinal agents.

This application is a continuation-in-part of our prior, copeudingapplication Serial Number 339,934, filed March 2, 1953, now abandoned.

The compounds of the present invention have the formula OKs-H 0 CH2 CH:C

wherein R is an alkylene radical having six carbon atoms in the carbonchain thereof and R is a member selected from the group consisting ofhydrogen and hydroxyl.

The compounds of the present invention are useful therapeutic agents byvirtue of their anti-stress activity. Thus the compounds of the presentinvention by systemic or oral administration exert a desirableanti-inflamatory efiect upon such diseases as gout, collagen disease,arthritis, rheumatism and rheumatic fever. They also inhibit allergenicand immune reactions, e.g. such as occur in heterologous transplat oftissues.

The compounds of the present invention are useful aids in devising newpharmacological tests for cortisonelike agents; thus when rats are usedas the test animal, a new test will not prove useful unless theinflammation or other signs of stress produced in the test are markedlyreduced by the oral or intraperitoneal administration of 10 to 100mgm./kg., e.g. as a 5 to 50% w./w. suspension in water containing 4% gumacacia or 0.5% carboxymethylcellulose.

Further understanding of the present invention is obtained by referenceto the following examples.

Example I A solution of isophorone (138.2 grams, 1.0 mole) in 200 ml.benzene is added dropwise to a stirred suspension of 39.0 grams (1.0)mole) sodium amide in 500 ml. benzene. Heat is applied and ammonia isevolved. The isophorone is added over about one hour and stirring andrefluxing is continued for another two hours. A solu tion of1,6-dibromohexane (122.0 gram, 0.5 mole) in 100 boils at about 157-l95C. at one mm., crystallizes on cooling and melts at about 60.5 -62.0 C.(64.5 -66.0 corrected) after repeated recrystallization, as fromSkellysolve B or methanol.

Analysis.-Calculated for C H O Calculated The product shows a positivequalitative test for ketones.

Example [I The product of Example I is converted into a compound havingthe formula by the method of Treibs, Berichte 66B, 1483 (1933), ofperacid oxidation followed by hydrolysis.

We claim:

The compound having the formula 0 0 ll II References Cited in the fileof this patent Rupe et al.: Helv. Chim. Acta, vol. 2, pp. 221-228(1919).

Beilstein, vol. 7 (2nd supplement), p. 565 (1948).

